moderate
2–3 hours
Moderate walking fitness required; ability to climb stairs comfortably.
Discover Chicago’s architectural wonders inside and out on a walking tour that reveals breathtaking interior details and sweeping skyline views. Explore the city’s iconic design from elevated vantage points and hidden indoor gems.
Special Access to Unique Views! • 2 Hours Long • All Ages
We get asked ALL THE TIME, "Where do we go to get a good high-up view of the city?" You could purchase expensive tickets to go wait in a long line at some tourist-treadmill observatory that everyone else knows about (and will be at). Or, you can join Inside Chicago Walking Tours on a high-up and low-down exploration of some personally curated favorite spots that give you beautiful, unique views, all for one low ticket price! No lines, no impersonal service, no cookie-cutter photos to bring back home. Come join Inside Chicago Walking Tours on a unique, exciting urban adventure!
Company founder and head tour guide, Hillary, introduced this tour route in 2017 after wanting to launch it since she started her business in 2014. Having formed friendly relationships with building staff and management in many spots downtown, as well as a solid reputation for quality tours and very satisfied customers, she is now able to welcome guests to special access granted by a handful of buildings to secret, amazing views of the city!
On this popular tour route, Inside Chicago Walking Tours will show you not only the stunning secret views from high up, but also the fascinating and fun views from down low. This tour is all about exploring the levels of downtown Chicago, from high up to ground level — and beyond!
2 Hours ~1.5 miles on foot
This tour covers several city blocks with occasional stairs inside buildings, so supportive shoes are recommended.
Meeting spots can be busy; arriving 10 minutes early helps ensure a smooth start.
Capture intricate interior details and expansive skyline shots from observation points.
Some viewpoints are outdoors; dress accordingly for Chicago’s variable weather.
Chicago pioneered the modern skyscraper in the late 19th century, deeply influencing global architectural trends.
Tours encourage sustainable urban tourism by limiting group sizes and promoting respect for historic structures.
Necessary for navigating city streets and building interiors with ease.
Chicago spring weather can be cool and windy, layers keep you comfortable.
spring specific
Protect your eyes during outdoor portions of the tour under strong sun.
summer specific
Fall showers can be frequent; come prepared to stay dry.
fall specific